Process for improving the crease resistance and the abrasion resistance of a textile material

ABSTRACT

This invention provides new condensation products which are obtained by reacting a monocyclic or dicyclic heterocyclic compound having 5 to 7 ring members, at least two members being nitrogen and at least two halogen atoms being linked directly with the carbon atoms of the hetero ring, with a thiourea compound, an alkali metal or ammonium hydrogensulfide and a monoor dialkanolamine. These condensation products are useful in combination with aminoplast precondensates for improving the crease resistance and the abrasion resistance of a textile material.

United States Patent [1 1 Buehler et a1.

[ PROCESS FOR IMPROVING THE CREASE RESISTANCE AND THE ABRASIONRESISTANCE OF A TEXTILE MATERIAL [75] Inventors: Arthur Buehler,Rheinfelden; Hans Ulrich Schuetz, Basel; Dieter Maeusezahl, Allschwil;Melvin Harris, Arlesheim; Christian Guth, Basel, all of Switzerland [73] Assignee: Ciba Limited, Basel, Switzerland [22] Filed: Jan. 5, 1971[21] Appl. No.: 104,142

Related US. Application Data [63] Continuation of Ser. No. 768,495, Oct.17, 1968,

abandoned. I

[30] Foreign Application Priority Data Oct. 24, 1967 Switzerland14826/67 52 us. (:1. 117/139.4, 117/138.8 F, 117/1395 A, 117/143 A 51Int. Cl D06m 13/00 [58] Field of Search 117/1394, 139.5 A, 117 143 A,138.8 F; 260/2498, 249.5, 249.6

[56] References Cited UNITED STATES PATENTS 2,561,973 7/1951 Cohen117/139.4X

[4 1 Dec.'4, 1973 2,573,525 10/1951 West 260/2498 X 2,684,346 7/1954Nickerson 117/1394 X 2,990,298 7/1961 Moyse et al. 117/1395 A 3,028,2644/1962 Frick l17/139.4 3,054,792 9/1962 Howard et al. 260/2498 X PrimaryExaminer-Murray Katz Assistant ExaminerTheod0re G. Davis Attorney-HarryGoldsmith, Joseph G. Kolodny, Bryant W. Brennan and Edward .1. Sites[57] ABSTRACT 6 Claims, No Drawings I PROCESS FOR IMPROVING THE CREASERESISTANCE AND THE ABRASION RESISTANCE OF A TEXTILE MATERIAL Thisapplication is a continuation of Ser. No. 768,49- 5, filed Oct. 17,1968, and now abandoned.

It has been found that valuable new condensates are obtained that arecapable of substantially counteracting the impairment of the mechanicalproperties occurring when finishing cellulosic textile materials withaminoplasts, when in an aqueous medium at a temperature from l to +30 C,in each case at a molecular ratio ofl :2 to 1 10.5, preferably from 11.5 to 1 10.5, a colourless heterocyclic compound that contains at least2 nitrogen atoms in the hetero ring and at least 2 halogen atoms linkedwith carbon atoms of the hetero ring, is reacted with A. a thioureacompound that contains at least one hydrogen' atom linked with nitrogen,preferably thiourea itself, or with an alkali metal or ammoniumhydrogensulphide and B. a monoor di-alkanolamine containing 1 to 4carbon atoms, preferably with monoor diethanolamine, the reaction isthen finalized at a temperature from 30 to 100 C, preferably from 45 to70 C and, if desired, water is distilled out of the mixture formed.

The heterocyclic compound used as starting material in the presentprocess must be practically colourless and contain at least one,preferably only one, heterocycle which may be altogether the only ringof the compound or, for example, may also contain a fused-on aromaticsix-membered' ring. Specially useful are compound with six-memberedhetero rings, especially those whose ring contains 2 or 3 nitrogen atomsand 4 or 3 carbon atoms, such as pyridazine, pyrimidine, quinazoline andespecially 1,3,5-triazine compounds. These compounds contain at least 2halogen atoms linked with carbon atoms of the hetero ring, for examplebromine or preferably chlorine atoms. As relevant examples there may bementioned trichlorpyrimidine, tetrachloropyrimidine,2,4-dichloroquinazoline, 2,4,6-tribromo-l,3,5-triazine and in the firstplace 2,4,6-trichloro-l,3,5-triazine (cyanuric chloride).

As further starting materials there are required a thiourea compoundcontaining at least one hydrogen atom linked with nitrogen, orpreferably thiourea itself or an alkali metal or ammoniumhydrogensulphide, as well as a monoalkanolamine or dialkanolaminecontaining l to 4 carbon atoms, preferably monoor diethanolamine.

The reaction is performed in an aqueous medium that may contain apartfrom water organic solvents, especially those which are water-miscible.There may be mentioned lower alcohols and acetone.

No specific sequence of the reaction stages is prescribed, that is tosay the heterocyclic compound may be reacted first with thesulphur-containing compound or first with the alkanolamine.

Forthe reaction'of every mol of component (A) or (B) with theheterocyclic compound 1 mol of alkali or a slight excess in form of anaqueous alkali metal hydroxide'or carbonate solution is added to thereaction mixture, either in one lot or portionwise.

The reactions are performed within the temperature range from --l0 to+30 C; in the presence of an organic solvent the reaction temperaturemay be below 0 C, whereas when purely aqueous reaction media are used itis advantageous to react at 0 C or slightly higher.

It is advantageous to start with the second reaction step in each caseonly after the first reaction is substantially complete; this isapproximately the case when after addition of the alkali, or of its lastportion, the reaction medium reveals a pH value of about 7. The reactionis then finalized at a temperature from 30 to 100 C, preferably from 40to 70 C, and may be terminated after 2 to 3 hours. The pH value of thereaction mixture during this time should be within the neutral orslightly alkaline region. A dropin pH value impairs the solubility ofthe reaction product substantially and can be prevented by adding morealkali. The condensates are also obtained, when in an aqueous medium ata temperature from 10 to +25? C at a pH value from 6 to 9 and at amolecular ratio from I 1.5 to l 0.5, a colourless heterocyclic compoundthat contains at least 2 nitrogen atoms in the hetero ring and at least2 halogen atoms linked with carbon atoms of the hetero ring, is reactedwith a thiourea compound and on completion of this first reaction stage,without intermediate separation, for every mol of heterocyclic halogencompound used 0.5 to 1.5 mols ofa monoalkanolamine'are added, whilemaintaining a pH value from 6 to 10 and keeping the temperature of thereaction medium first for at least 8 hours at 30 to C and then for atleast 5 hours at to C and, if desired, the water is distilled out of themixture formed.

When the starting material used is cyanuric chloride, then, in general,for 1 mol each of this halogen compound a total of about 4 mols ofmonoacidic base, thus for instance 3 mols of alkali metal hydroxide andlmol of alkanolamine, is consumed. The amount of water used as reactionmedium may be freely chosen within a wide range, advantageously so that,on one hand, the reaction mixtureis easy to stir from the start and therisk of heating beyond the prescribed temperature range is obviated andthat, on the other hand, excessive dilution does not make the practicalperformance problematic. Since as a rule the heterocyclic halogencompounds are sparingly soluble in the water serving as reaction medium,it is advantageous first to convert them into a finely distributedstate, which can be done in known manner by dissolution in an organicwatermiscible solvent such as acetone and pouring the solution out overice, As mentioned above, the molecular ratio heterocyclic halogencompound sulphurcontaining compound should range from 1 2 to l 0.5,preferably from 1 11.5 to l 0.5, and the molecular ratio of heterocyclichalogen compound alkanolamine should likewise be within the range from 12 to 1 0.5, preferably from 1 l.5 to l 0.5. Especially with cyanuricchloride particularly good results are obtained by using equimolecularproportions or amounts of the three reactants differing only littletherefrom.

On completion ofthe reactionthe resulting product can be used as it isfor thepurpose indicated above. In view of the concentration of themixture, which is not very high at the end of the reaction, it is,however, advisable to remove the water completely or partially bydistillation under vacuum. In this manner generally stable products areobtained which are at most only slightly tinted and are readily andcompletely soluble in water.

The products obtained by the process described above are suitable, ashas already been said, for use in combination with aminoplasts intextile finishing, especially for improving the shape retention.Particularly suitable for such a treatment is textile material ofcellulose, if desired in combination with other fibres, for examplepolyester fibres. Therefore, according to a preferred use of theproducts of this invention textile materials are impregnated with anaqueous preparation containing a curable aminoplast precondensate, acuring catalyst and a condensate of the composition defined above,whereupon the textile material is dried and hardened by treatment at anelevated temperature.

Aminoplast precondensates are adducts of formaldehyde with methylolablenitrogen compounds. In this connection there may be mentionedamino-1,3,5- triazines such as N-substituted melamines, for exampleammeline, guanamines, for example benzoguanamine or acetoguanamine.Further suitable are symmetric alkyltriazones, biuret, thiourea,alkylcarbamates, guanidine, alkylor aryl-ureas and -thioureas, alkyleneureas or diureas, for example ethyelne urea, propylene urea or acetylenediurea; 4,5-dihydroxy-imidazolidone-2 and its derivatives, for examplethe 4,5-dihydroxyimidazolidone-Z substituted in 4-position on thehydroxyl group by the residue CH CH CON- H-CH -OH. The methylolcompounds of urea and of melamine are preferred and in the case ofmelamine compounds those ofa low or high degree of methylolation may beused. It is also possible to use compounds whose methylol groups aremore or less completely etherified, for example, with methyl groups.

As curing catalysts the conventional acid or potentially acid compoundsmay be used, such as ammonium chloride, magnesium chloride or zincfluoroborate.

Particularly valuable results are also obtained when the preparationused for finishing the textile materials contains in addition to theaminoplast precondensate, the curing agent and the condensate of thisinvention also an emulsion polymer prepared from an N- methylolamide ofan a,B-ethylenically unsaturated carboxylic acid or an ether of such amethylolamide and an alkaline earth metal salt of an a,,B-ethylenicallyunsaturated monocarboxylic acid, especially the copolymers, obtained inan aqueous emulsion, from a. 0.25 to percent by weight of an alkalineearth metal salt of an a,,B-ethylenically unsaturated monocarboxylicacid (for example calcium acrylate),

b. 0.25 to 30 percent by weight of an N- methylolamide orN-methylolamide ether of an a,B-unsaturated monoor dicarboxylic acid(for example acrylic acid methylolamide, methacrylic acid methylolamideor the methyl ethers of these methylolamides),

c. 99.5 to 60 percent by Weight of at least one further copolymerizablecompound, for example an ester of acrylic or methacrylic acid and analkanol such as methanol, ethanol, n-butanol, acrylic acid tertiarybutylamide, vinylidenechloride, vinylacetate, acrylonitrile, styrene.

Depending on the purpose to be served by the finish the aqueouspreparations may contain further ingredients, for example hydrophobizingagents, suitable optical brighteners, wetting agents, dispersants orflameproofing agents, especially phosphorus compounds such asdialkylphosphono-propionic acid methylolamides. In very many cases it isalso advisable to add, for example, a nonionic agent that produces asoft handle,

for example an aqueous emulsion of a methylolmelamine alkyl ethermodified by stearic acid alkylolamide residues.

The proportions of the ingredients of the aqueous preparations may varywithin wide limits and may be adapted to the purpose in hand. In generalit is indicated to use for 10 parts of aminoplast precondensate 1 to 4parts of condensate from heterocyclic halogen compound, thiourea andalkanolamine. Otherwise, the textile material may be treated in theusual manner. For example, undyed or dyed fabric or tricot may beimpregnated on a padder with the preparation and, advantageously afteran intermediate drying operation at a temperature of up to 100 C,subjected to a treatment with dry heat of l-l80 C for 2 to 20 minutes,the temperature and the duration of the treatment being adapted to thepurpose of the treatment which may be, for example, an improvement ofthe wet fastness properties for direct dyeing dyestuffs, an anti-creasefinish or permanent shaping (permanent press). The finishing operationmay also be combined with a dyeing operation, for example so that theimpregnating solution further contains a dyestuff which, by virtue ofspecial substituents, is reactive towards the fibre or more especiallytowards the aminoplast precondensate and, by virtue of this property, isfixed on the substrate during the heat treatment or even before it.

As is known an aminoplast resin finish impairs the mechanical propertiesof cellulosic fibrous materials, especially their tensile strength andabrasion resistance; in general the loss in strength is the greater thehigher the content of aminoplast and the more energetic the hardeningis. As mentioned above, these serious drawbacks can be substantiallyprevented with the aid of the new condensates or at least they can bereduced to an acceptable degree. In addition it has been observed thatthese condensates improve the soil release from the fibre.

Example 1 A solution of 190 g (1 mol) of cyanuric chloride in 1 litre ofacetone is poured over a mixture of 1 litre of water and 1 kg of ice andthe precipitated cyanuric chloride is filtered off. The paste isintroduced into a solution which has been prepared at C from 76 g (1mol) of thiourea and one-half litre of water and has then been cooled byadding one-half kg of ice. By dropping in a 5N-sodium hydroxide solutionthe pH value is maintained at 6.7 to 6.9 during this first condensationstage and the temperature is maintained at 8 to 10 C by indirectcooling. After about 5 hours and a consumption of about 3.5 mols ofsodium hydroxide the pH value remains constant, and practicallyeverything is dissolved in the reaction mixture. Then one lot of 61 g (1mol) of monoethanolamine is added and the solution, which is now clear,is heated in a second condensation stage for 15 hours at 35 to 40 C andin a third stage for 8 hours at to C. During this time further sodiumhydroxide solution is added as and when required so that the pH valueremains constant at 7.0, for which about 0.5 mol of sodium hydroxide isneeded. Finally, the solution is evaporated to dryness at to C undervacuum and the residue is ground in a ball mill, to furnish 410 g of afaintly yellowish, readily water-soluble hygroscopic powder condensateA.

. 5 Apart from product A the following Table lists further condensatesobtained in this manner, together with the appropriate data for theirmanufacture:

g (0.05 mol) of anhydrous sodium carbonate in 15 ml of water during 1hour the pH value of the reaction mixture is maintained at about 7.

TABLE I Quantity in mols 1st stage 2nd stage 3rd stage Working up E=Cyan- Ethevaphrate uric ThlanolpH- pH- pH- in a uo chloride ourea amineTemp. Hours value Temp Hours value Temp. Hours value at C.

A 1 1 1 8-10 5 6. 76.0 35-40 15 7 55-60 8 7 E -100 B. 1 1 1 0-10 86.0-6. .35-40 14 7 55-60 J 7 E 00-100 C 1 1 1 0-12 2 8-9 35-40 15 755-60 8 7 E 90-100 D 1 1 1 0-10 4% 7 35-40 15 7 55-60 8 7 E 90-100 E 1 11 0-8 5 7 35-40 14 7 55-60 0 7 E 00-100 F 1 1.5 0.5 0-10 8 7 35-40 13 755-60 7 7 E 00-100 G 1 0. 5 1. 5 0-10 22 7 35-40 22 7 55-60 8 7 H 2 2 20-12 14 7 35-40 18 7 55-60 8 7 E 90-100 1 Filter off insol. residue thenE 90-100.

E l 2 Then 7.6 g (0.1 mol) of thiourea and 20 ml (0.1 mol) A solution of18.5 g (0.1 mol) of cyanuric chloride in 100 cc of acetone is poured outover a mixture of 0.1 litre of water and 0.1 kg of ice, and theprecipitated cyanuric chloride filtered off. The paste is introducedinto a solution which has been prepared at 45 C from 7.6 g (0.1 mol) ofthiourea and 50 ml of water and then cooled by adding 50 g ofice'thereto. in this first condensation stage the pH value is maintainedat 6.7 to 6.9 by dropping in a SN-sodium hydroxide solution and thetemperature is kept at 8 to C by indirect cooling.

After about 5 hours and a consumption of about 3.5 mols of sodiumhydroxide the pH value remains constant and practically all hasdissolved in the reaction mixture. One lot of 10.5 g (0.1 mol) ofdiethanolamine is then added and the reaction mixture heated to 55 to 60C while adding another 10 ml of 5N-sodium hydroxide solution (0.05 mol)and then heated at this temperature with stirring for 5 hours. i

The solution is then evaporated to dryness at 60 C under vacuum, toyield 46 g of a pale yellowish, readily water-soluble powder: condensateJ.

Example 3 A suspension of 18.5 g (0.1 mol) of cyanuric chloride in 100ml of alcohol is cooled to 5 to 10 C. One lot of 6.1 g (0.1 mol) ofmonoethanolamine is added; dur ing minutes m1 of SN-sodium hydroxidesolution (0.1 mol) are dropped in and the reaction mixture is stirredfor about 1 hour at the same temperature until a constant pH value ofabout 2.7 has been established.

On addition of 7.6 g (0.1 mol) of thiourea and 30 ml of 5N-sodiumhydroxide solution (0.15 mol), in each case in one lot, the pH value ofthe reaction mixture temporarily reaches 1 l which'drops again to 7after another 30 minutes reaction, during which the temperature israised to 30 to 40 C. Then another 20 ml of SN-sodium hydroxide solutionare added and the reaction terminated after stirring for 2 /2 hours.

The resulting colourless suspension is evaporated to dryness at 40 Cunder vacuum, to leave 40 g of a pale yellow, readily water-solubleproduct: condensate K.

Example 4 v 18.5 Grams (0.1 mol) of cyanuric chloride are suspended in200 ml of a mixture of 100 ml of water and 100 ml of acetone and at 0 C6.1 g (0.1 mol) of monoethanolamine are added in one lot. By dropping in5.3

of SN-sodium hydroxide solution are added. When the pH value has droppedto 7, the temperature is raised to 50 C and the reaction finalized bystirring for minutes, during which another 40 ml (0.2 mol) of 5N- sodiumhydroxide solution are gradually added. The resulting reaction mixtureis evaporated to dryness under vacuum, to yield 40 g of a readilywater-soluble condensate: condensate L.

Example 5 A suspension of 18.5 g (0.1 mol) of cyanuric chloride in ml ofwater is mixed within 60 minutes at 0 C with 14.35 ml (0.1 mol) of a39.1 percent solution of sodium hydrosulphide.

The resulting yellow suspension is mixed' at room temperature with 6.1 g(0.1 mol) of monoethanolamine and then with one lot of 20 ml (0.1 mol)of 5N-sodium hydroxide solution. The batch is then heated to 50 C andheated and stirred at this temperature for about 2 hours. After thistime the reaction mixture reveals a pH value of about 7.

Another 20 ml (0.1 mol) of 5N-sodium hydroxide are added and thereaction continued for 3 hours at the same temperature, whereupon it isterminated, and the pH value adjusts itself at 10. The reaction mixtureis first filtered to remove the insoluble components (5.5 g of ayellowish substance) and the filtrate is then evaporated to dryness at60 C under vacuum, to yield 26.5 g of a white powder: condensate M.

Example 6 Aqueous padding liquors are prepared with the use of thesubstances listed below:

a. Aminoplast precondensate 50 percent aqueous solution of a mixture ofdimethylolethylene urea and methyl ether of a highly methylolatedmelamine.

b. Softening agent 30 percent aqueous dispersion of a methyl ether(modified with stearic acid alkanolamides) of a highly methylolatedmelamine.

c. Copolymer 27 percent aqueous emulsion of a copolymer from 80 parts ofacrylic acid n-butyl ester, 13 parts of vinylidenechloride, 6 parts ofacrylic acid methylolamide and 1 part of calcium acrylate.

d. Condensate prepared as described in Example 1 from cyanuric chloride,thiourea and monoethanolamine: condensate A.

Mercerised and bleached cotton popelin is then impregnated with paddingliquors, whose composition is TABLE II (a) Aminoplast precondens e,g.(b) Softening agent, gJl (c) Copolymer emulsion,

(d) Condensate A, g./l M 'Cl2-6lI20, tl./l C 'I;CO01'I,40% g. pH ofpadding liquor Tens. strength, percent Abrasion res, percent Creaseresist. in Crease angle, wet in HN-CHz-CIhS O aNa number of abrasiverotations (n) are counted that are needed to hole the tested material,after having ascertained this number with untreated material (in). Fromthe results obtainedthe abrasion resistance values (A) of the treatedfabric specimens are calculated: A lOOn/m. (3), (4) To determine thecrease angle dry and evenly moistened rectangular pieces of fabric, cutdiagonally across the fibres, measuring 16 mm X 44 mm are foldedparallel to the short side, placed in between glass plates and loadedwith 2 kg-weights. After 5 minutes loading and l hours recovery the testspecimens are introduced into an angle measuring instrument ofconventional design and the crease angle is measured.

Example 7 Mercerized cotton popelin is impregnated with the liquors ofthis composition, then dried at 60 to 80 C and heated for 13 minutes at170 C. The fabric is then washed for 5 minutes in a boiling 0.2 percentsodium carbonate solution, rinsed in cold water and dried.

TABLE III.

(a) Aminoplast precondensate, g./l 140 140 140 30 nil-value of paddingliqu0r. 5.1 Tensile strength, percent 52 Abrasion resistance, percent 48Crease angle, dry, in degrees 132 Crease angle, wet, in degrees 4 11!)NOTE.Concerning 1, 2, 3 and 4: The measuring of these vulues has beenexplained following upon Table 11.

Example 8 Aqueous padding liquors are prepared with the use of theunder-mentioned substances:

a. Aminoplast precondensate 50 percent aqueous solution ofa mixture ofdimethylol-ethylene urea and methyl ether of a highly methylolatedmelamine.

b. Softening agent 30 percent aqueous dispersion of a methyl ether(modified with stearic acid alkanolamides) of a highly methylolatedmelamine.

c. Copolymer 27 percent aqueous emulsion of a copolymer from 80 parts ofacrylic acid n-butyl ester, 13 parts of vinylidenechloride, 6 parts ofacrylic acid methylolamide and 1 part of calcium acrylate.

d. Wetting agent 25 percent aqueous solution of an adduct ofp-nonylphenol with 9 mols of ethylene oxide.

e. Brightening agent of the formula S OaNa (LCM f. One of the followingcondensates:

l. Condensate from cyanuric chloride, thiourea and monoethanolamine,prepared according to Example I: condensate A.

2. Condensate from cyanuric chloride, monoethanolamine and thiourea,prepared according to Example 3: condensate K.

3. Condensate from cyanuric chloride, sodium hydrogensulphide andmonoethanolamine, prepared according to Example 5: condensate M.

g. Magnesium chloride hexahydrate (MgCl '6H O).

Mercerized and bleached cotton popelin is impregnated with paddingliquors composed as shown in Tables IV, V and V1 to a weight increase of60 percent referred to the original weight of the fabric. After havingbeen dried at 60 to 80 C the fabric is heat-treated for 4% minutes at C,then washed for 5 minutes in a boiling 0.2 percent sodium carbonatesolution, rinsed in cold water and dried.

TABLE IV TABLE IV I Continued (g) MgClz-fiHzO, g./l 15 15 15 pH-value ofthe padding liquor 5. 9 5.9 5. 9 5. 9 Tensile strength, percent .100 6369 Abrasion resistance, percent 2 100 19 59 39 103 Crease angle indegrees:

Dry 3 53 133 122 130 127 (b) Wei; 4 65 116 121 124 126 Nornto Thesevalues are measured as described following Table TABLE V (a) Aminoplastprecondensate, g./l 150 15 (b) Softening agent, g./l 1 30 30 30 39 (e)Copolymer emulsion, g.ll 40 40 (d) Wetting agent, g./l t t. 3 3 3 3 (e)Brightening agent, g./l. 3 3 3 3 (i) Condensate K, g./l a a 5 (g)MgClz-fiHzO, g./l 15 15 15 15 pH-value of the padding liquor 5. 9 5. 95. 9 5.9 Tensile strength, percent 100 63 69 63 72 Abrasion resistance,percent 2 100 19 55 39 8B Crease angle in degrees- Dry 3 53 133 123 130120 (b) Wet 65 116 120 124 117 Norato These values are measured asdescribed following Table 11.

TABLE VI (a) Aminoplast precondensate, g./l 150 150 150 150 (b)Softening agent, g./l 30 30 30 30 (c) Copolymer emulsion, g./l 40 40 (d)Wetting agent, g./l 3 3 3 3 (e) Brightening agent, g./l-. 3 3 3 3 (f)Condensate M, g./l 10 (g) MgClzJiHzO, g-ll 15 -15 15 pH-velue of thepadding liquor. 5. 9 5. 9 5.9 5. 9 Tensile strength, percent 1 100 63 5963 71 Abrasion resistance, percent 2 100 19 48 39 94 Crease angle indegrees:

Dry 5 53 133 119 130 127 (1)) Wet 65 116 119 124 126 IINo'rE. to Thesevalues are measured as described following Table We claim: 1. In theprocess for improving the crease resistance and the abrasion resistanceof a textile material by impregnation with an aqueous preparationcontaining a thiourea, sodium-, potassiumand ammonium hy- Idrogensulfide, and

C. a member selected from the group consisting of a monoalkanolaminc anda dialkanolamine with l to 4 carbon atoms in an aqueous medium at atemperature from about 10 to 30 C at a molecular ratio for (B) as wellas for (C) from l:2 to 1:05, then finalizing the reaction attemperatures from 30 to C and removing water from the resulting mixtureby distillation.

2. Process according to claim 1, wherein the initial alkanolamine usedto obtain the condensation product is monoethanolamine ordiethanolamine.

3. Process according to claim 1, wherein to obtain the condensationproduct the molecular ratio of cyanuric chloride to component (B) and(C) is from 1:15 to 1:05.

4. Process according to claim 1, wherein the aminoplast precondensate isa methylol compound of urea or melamine.

5. Process according to claim 1, wherein the impregnating the textilematerial condensation product is obtained by reacting cyanuric chloridewith A. thiourea in an aqueous medium at a temperature from about- 10 to25 C and at a-pH- value from 6 to 9 at a molecular ratio of 121.5 to1:0.5 and, without intermediate separation with (B) 0.5 to 1.5 mols of amonoalkanolamine with l to 4 carbon atoms for every mol of cyanuricchloride, maintaining a pH-value from 6 to 10, keeping the temperatureof the reaction for at least 8 hours at 30 to 50 C and then for at least5 hours at 60 to 65 C, and removing water from the resulting mixture bydistillation.

6. Process according to claim 1, wherein the aminoplast precondensatecomprises an adduct of formaldehyde with a nitrogen compound reactabletherewith to form an N-methylol group, the curing catalyst is an acid orpotentially acid compound, drying is effected at a temperature up to 100C and heating is effected with dry heat at a temperature from to C for20

2. Process according to claim 1, wherein the initial alkanolamine usedto obtain the condensation product is monoethanolamine ordiethanolamine.
 3. Process according to claim 1, wherein to obtain thecondensation product the molecular ratio of cyanuric chloride tocomponent (B) and (C) is from 1:1.5 to 1:0.5.
 4. Process according toclaim 1, wherein the aminoplast precondensate is a methylol compound ofurea or melamine.
 5. Process according to claim 1, wherein theimpregnating the textile material condensation product is obtained byreacting cyanuric chloride with A. thiourea in an aqueous medium at atemperature from about-10* to 25* C and at a pH- value from 6 to 9 at amolecular ratio of 1:1.5 to 1:0.5 and, without intermediate separationwith (B) 0.5 to 1.5 mols of a monoalkanolamine with 1 to 4 carBon atomsfor every mol of cyanuric chloride, maintaining a pH-value from 6 to 10,keeping the temperature of the reaction for at least 8 hours at 30* to50* C and then for at least 5 hours at 60* to 65* C, and removing waterfrom the resulting mixture by distillation.
 6. Process according toclaim 1, wherein the amino-plast precondensate comprises an adduct offormaldehyde with a nitrogen compound reactable therewith to form anN-methylol group, the curing catalyst is an acid or potentially acidcompound, drying is effected at a temperature up to 100* C and heatingis effected with dry heat at a temperature from 140* to 180* C for 20 to2 minutes.